Adsorption behavior of end-functionalized polymers modified by iminium ion

Furusawa, Kunio; Ogawa, Toshiki; Itabashi, Tadashi; Miyahara, Tomoko; Kitahara, Shizuo; Kawanaka, Tomohiro

doi:10.1007/bf00664718

Cited by 9 publications

(4 citation statements)

References 7 publications

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“…The monodisperse polystyrenes (PS) and their terminal-functionalized ions (PS-X) were supplied by Nihon Zeon Co., Ltd., Japan. PS-X was synthesized by the anionic polymerization technique and one end of the chain terminates with an iminium cation. − The characterization data of the polymer samples are shown in Table .…”

Section: Methodsmentioning

confidence: 99%

“…Adsorption and Desorption Experiments. Each polymer was adsorbed on the alumina powders by the usual depletion technique in cyclohexane solution. , Alumina powder and a cyclohexane solution of polymer were added in a glass tube (10 mL in volume) and the tube was agitated slowly in a water bath maintained at 35 °C (the θ condition of polystyrene in cyclohexane). After some adsorption time (0−120 h), the adsorbent particles covered by the polymer layers were packed into a Teflon tube (20 cm, 0.8 mm i.d.)…”

Section: Methodsmentioning

confidence: 99%

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Desorption Behavior of (Terminal-Functionalized) Polystyrenes from Alumina Surfaces. Studied by the Continuous Elution Method

Chen

Furusawa

1996

Langmuir

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To explore the desorption behavior of polymers from the solid surfaces, a new experimental technique was introduced in this research. We referred to it as the “continuous elution method”. Using this method, the desorption behavior of preadsorbed polystyrene (PS) and polystyrene (PS-X) functionalized by a terminal iminium ion (X) from α- and γ-alumina surfaces was investigated. The particles preadsorbed by PS or PS-X were packed into a small column and eluted by various solvents. Irreversibility of polymer adsorption can be observed clearly, the adsorption/desorption amount can be determined, and much new information on kinetics of desorption, adsorption energy, solvency effect, and etc. was also obtained. On α-alumina, it was found that only the X-group is the driven force for adsorption, and the adsorbed layer has a higher energetic state than that on γ-alumina. A complicated desorption kinetics of polymer desorbed from γ-alumina was observed, which has a relation to the porosity of adsorbent.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Desorption Behavior of (Terminal-Functionalized) Polystyrenes from Alumina Surfaces. Studied by the Continuous Elution Method

Chen

Furusawa

1996

Langmuir

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“…Furusawal et al. studied an iminium ion end‐group‐functionalized polymer . Furthermore, there are many examples of linear poly(azomethines) reported, which can potentially react with electrophiles to iminium structures.…”

Section: Introductionmentioning

confidence: 99%

Radical Copolymerization of N‐Vinylformamide with Methylvinylketone: An Approach to Iminium/Imine Ring Containing Polymers

Walther

Seifert

Hähnle

et al. 2018

Macro Chemistry & Physics

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The free radical copolymerization of N‐vinylformamide (NVF) with methylvinylketone in water and the subsequent alkaline or acidic hydrolysis produce iminium structures containing polymers. It can be concluded from the copolymerization parameters (rN ‐vinylformamide = 0.02, r methylvinylketone = 0.50) that alternating copolymers are formed which contain few amounts with statistically arranged monomer sequences. The acidic hydrolysis of the copolymer results in a water‐soluble polymer bearing five‐membered iminium rings along the polymer chain. A water‐insoluble polymer is generated under alkaline conditions also containing five‐membered imine rings. The formation of the iminium ring polymer is attributed to the fact that generated free amino groups derived from NVF immediately react with the keto groups in the vicinity. The molecular structures of the obtained polymers are characterized by 1H‐NMR, 13C‐NMR, and IR spectroscopy. The assignment of the signals in the novel polymers are confirmed by model compounds.

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“…16 Also the IR of the solid dyes showed a band at 1660 cm −1 relating to the iminium group. 16,25 In divinylbenzene (DVB) cross-linked polystyrene resins residual alkenes from DVB may be present from incomplete polymerization. 26 These reactive alkenes may react with the enamine formed from the secondary amine so that no additional Fmoc-amino acid is needed to induce coloring in this case.…”

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confidence: 99%

Color Test for Selective Detection of Secondary Amines on Resin and in Solution

Boas

Mirsharghi²

2014

Org. Lett.

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Resins for solid-phase synthesis give orange to red-brown resin beads selectively when secondary amines are present on the resin when treated with a solution of acetaldehyde and an Fmoc-amino acid in NMP. The method shows good specificity and gives colorless beads when exposed to a variety of other functional groups. Furthermore, the acetaldehyde/Fmoc amino acid method can be used as a selective colorimetric test for secondary amines in solution.

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Adsorption behavior of end-functionalized polymers modified by iminium ion

Cited by 9 publications

References 7 publications

Desorption Behavior of (Terminal-Functionalized) Polystyrenes from Alumina Surfaces. Studied by the Continuous Elution Method

Desorption Behavior of (Terminal-Functionalized) Polystyrenes from Alumina Surfaces. Studied by the Continuous Elution Method

Radical Copolymerization of N‐Vinylformamide with Methylvinylketone: An Approach to Iminium/Imine Ring Containing Polymers

Color Test for Selective Detection of Secondary Amines on Resin and in Solution

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